Hydrochloric Acid → HCID 69216411, compound

HRID 2222036Notes

Reaction equation

HRID 2222036 reaction equation
C([O:3][C:4](=[O:62])[CH2:5][C:6]1[CH:11]=[CH:10][C:9]([C:12]2[O:13][C:14]([CH3:61])=[C:15]([CH2:17][O:18][C:19]3[CH:58]=[CH:57][C:22]([CH2:23][O:24][C:25]4[C:29](/[CH:30]=[CH:31]/[C:32]5[N:33]=[C:34]([N:38]6[CH2:43][CH2:42][N:41]([C:44]([O:46][C:47]([CH3:50])([CH3:49])[CH3:48])=[O:45])[CH2:40][CH2:39]6)[S:35][C:36]=5[CH3:37])=[CH:28][N:27]([C:51]5[CH:56]=[CH:55][CH:54]=[CH:53][CH:52]=5)[N:26]=4)=[CH:21][C:20]=3[O:59][CH3:60])[N:16]=2)=[CH:8][CH:7]=1)C.O1CCCC1.[OH-].[Na+].Cl>O.C(O)C>[C:47]([O:46][C:44]([N:41]1[CH2:42][CH2:43][N:38]([C:34]2[S:35][C:36]([CH3:37])=[C:32](/[CH:31]=[CH:30]/[C:29]3[C:25]([O:24][CH2:23][C:22]4[CH:57]=[CH:58][C:19]([O:18][CH2:17][C:15]5[N:16]=[C:12]([C:9]6[CH:10]=[CH:11][C:6]([CH2:5][C:4]([OH:62])=[O:3])=[CH:7][CH:8]=6)[O:13][C:14]=5[CH3:61])=[C:20]([O:59][CH3:60])[CH:21]=4)=[N:26][N:27]([C:51]4[CH:56]=[CH:55][CH:54]=[CH:53][CH:52]=4)[CH:28]=3)[N:33]=2)[CH2:39][CH2:40]1)=[O:45])([CH3:48])([CH3:50])[CH3:49]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 8028TetrahydrofuranHCID 14798Sodium HydroxideHCID 69216313HCID 69216313, compound

Product 1

HCID 69216411HCID 69216411, compoundYield 50%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Conditions

Temperature
50 °C

Procedure

To a mixture of tert-butyl 4-{4-[(E)-2-(3-{[4-({2-[4-(2-ethoxy-2-oxoethyl)phenyl]-5-methyl-1,3-oxazol-4-yl}methoxy)-3-methoxybenzyl]oxy}-1-phenyl-1H-pyrazol-4-yl)ethenyl]-5-methyl-1,3-thiazol-2-yl}piperazine-1-carboxylate (0.30 g), tetrahydrofuran (6 mL) and ethanol (3 mL) was added 1N aqueous sodium hydroxide solution (1 mL), and the mixture was stirred at 50° C. for 1 hr. To the reaction mixture were added 1N hydrochloric acid (1 mL) and water, and the mixture was extracted with ethyl acetate. The ethyl acetate layer was washed with saturated brine, dried over anhydrous magnesium sulfate and concentrated to give [4-(4-{[4-({[4-((E)-2-{2-[4-(tert-butoxycarbonyl)piperazin-1-yl]-5-methyl-1,3-thiazol-4-yl}ethenyl)-1-phenyl-1H-pyrazol-3-yl]oxy}methyl)-2-methoxyphenoxy]methyl}-5-methyl-1,3-oxazol-2-yl)phenyl]acetic acid as crystals (0.14 g, yield 50%). Recrystallization from ethyl acetate-hexane gave brown prism crystals. melting point: 119-120° C.

Workup

  1. extractionthe mixture was extracted with ethyl acetate
  2. washThe ethyl acetate layer was washed with saturated brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-ba62fa7d7e524e5abd0e34f401c69350
Source dataset
uspto-grants-2008_05
Patent number
US07368578B2

Reaction notes

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